I’ve worn red lipstick before, and have learned quickly the best shades for my skin tone. The general rule of thumb is to choose a red hue that matches your skin tone the best to get the most out of your daring shade.
If you have pale skin with pink undertones, or just very pale skin in general, you want to stick with red lipsticks that are purple or pink based to avoid a color that looks too brassy. Berry reds are best if you have pale skin, and shiny colors look less “out there” than mattes or flat colors. If you don’t want to go too red, choose a shine with glitter to reflect off the color and make you look less like the red is taking over your face and washing you out.
Orange and coppery reds look awesome on redheads (the exception to the pale color palate) and tan or medium-skinned individuals. Bright fire engine red clashes with the skin tone, but reds with gold flecks in them, reds with copper undertones, or orange reds work out great if you want to complement your more yellow-based skin tone.
Very dark skin can go with the darkest, most bold reds, and even black reds. Reds that are deep berry colored or very vibrant go great with these darker skin tones, and bring amazing color to the whole face.
It is important that if you are going to wear red lipstick to make sure not to overdo it on other areas of your face, such as too much eyeliner, mascara, or blush. You want to bring a focal point to your lips when wearing red to avoid looking too done up or costumey. If you are trepidacious about trying red out, go for a shimmery red or even a dusty pink that helps to urge you into the red zone, lipstick-wise, and if you try red and want to tone it down, go over the color with a sheer Chapstick and blot some off, or apply a nude color on top of red to make it stand out less. Above all, experiment to find the best red lipstick hue for you!